676556-29-9Relevant academic research and scientific papers
A new, highly stereoselective synthesis of β-unsubstituted (Z)-γ-alkylidene-butenolides using bromine as a removable stereocontrol element
Boukouvalas, John,Beltrán, Paola P.,Lachance, Nicolas,C?té, Sébastien,Maltais, Fran?ois,Pouliot, Martin
, p. 219 - 222 (2007)
Several β-unsubstituted (Z)-γ-alkylidenebutenolides have been prepared in highly stereocontrolled fashion by implementing a steric directing group stratagem in the vinylogous aldol condensation of butenolides with aldehydes. Applications to the synthesis of the antitumor heptene (S)-melodorinol and a thiophenelactone from Chamaemelum nobile L. are described. Georg Thieme Verlag Stuttgart.
METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
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Page/Page column 14; 15, (2011/08/06)
The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.
A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides
Sorg, Achim,Siegel, Konrad,Bru?ckner, Reinhard
, p. 321 - 325 (2007/10/03)
γ-(Dibromomethylene)butenolide (2) and β-bromo-γ- (bromomethylene)butenolide (Z-5), both of which obtained from dibromolevulinic acid (6) in a single step, underwent Pd-catalyzed couplings with phenyl- or styryltributylstannane giving mono-bromobutenolides with excellent stereo- and regiocontrol. A second Stille coupling or the reduction with Zn dust led to bromine-free γ-alkylidenebutenolides as single stereoisomers.
